Triethylamine → ethyl 2-[3-[4-(2-naphthamido)benzyl]-1H-indazol-1-yl]acetate

HRID 589349Notes

Reaction equation

HRID 589349 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[C:41](Cl)=[O:42].C(=O)(O)[O-].[Na+]>ClCCl>[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[C:41]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:8]=2)=[CH:22][CH:23]=1)=[O:42]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 516892Sodium BicarbonateHCID 89590284ethyl 2-[3-(4-aminobenzyl)-1H-indazol-1-yl]acetate

Product 1

HCID 89590254ethyl 2-[3-[4-(2-naphthamido)benzyl]-1H-indazol-1-yl]acetateYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

630 mg (2.04 mmol) ethyl 2-[3-(4-aminobenzyl)-1H-indazol-1-yl]acetate was dissolved in 20 mL dichloromethane. 0.85 mL (6.11 mmol) triethylamine was added, and in an ice bath a dichloromethane solution dissolving 428 mg (2.25 mmol) 2-naphthoyl chloride was added slowly, and reacted in an ice bath for 3 h. An aqueous solution of sodium bicarbonate was added to quench, extracted with ethyl acetate, rotate evaporated to dryness, chromatographed on a column to obtain a white solid 850 mg, at a yield of 89.7%.

Workup

  1. additionwas added slowly
  2. customreacted in an ice bath for 3 h
  3. customto quench
  4. extractionextracted with ethyl acetate, rotate
  5. customevaporated to dryness
  6. customchromatographed on a column

Sources & evidence

ORD record
ord-5957d1608b9e429da9ed099558e92951
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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